Various amino protecting groups influence on 1H and 13C chemical shifts in a 2-deoxy-2-amino glucopyranoside

One glycoside, pent-4-enyl 2-amino-3, 4-di-O-benzoyl-6-O-t-butyldimethylsilyl-2-deoxy-B-D-glucopyranoside (1), has been derivatized at the amino function into five related compounds: ammonium trifluoroacetate, N-acetyl, tetrachlorophthalimide, phthalimide and azide. The 1H and 13CNMR spectra of these compounds have been fully assigned and compared. Significant influence on the chemical shifts given by the amino functionality can be found in the pyranosidic ring at position 1, 2 and 3. Only minor variations were found throughout the remaining positions.